Organic Chemistry

Enantioselective Total Synthesis of the Archaeal Lipid Parallel GDGT-0

Abstract

Archaeal glycerol dibiphytanyl glycerol tetraethers (GDGT) are some of the most unusual membrane lipids identified in nature. These amphiphiles are the major constituents of the membranes of numerous Archaea, some of which are extremophilic organisms. Due to their unique structures, there has been significant interest in studying both the biophysical properties and the biosynthesis of these molecules. However, these studies have thus far been hampered by limited access to chemically pure samples. Herein, we report a concise and stereoselective synthesis of the archaeal tetraether lipid GDGT-0 and the synthesis and self-assembly of derivatives bearing different polar groups.

Content

Thumbnail image of GDGT0 ChemRxiv.pdf

Supplementary material

Thumbnail image of GDGT0 Supporting Info ChemRxiv_revised.pdf
GDGT0 Supporting Info ChemRxiv revised